Stadium: Center Court Round: 27 Ground: Hardcourt outdoor
| ITF - Heraklion M15 - MD | 2023/11/21 12:45 | Antonopoulos/Xilas v Tsitsipas/Tsitsipas | 1-6,4-6 |
| ATP Antwerp - MD | 2023/10/22 12:00 | Behar/Pavlasek v Tsitsipas/Tsitsipas | 7-6,4-6,8-10 |
| ATP Antwerp - MD | 2023/10/21 18:25 | Tsitsipas/Tsitsipas v Arneodo/Weissborn | 4-6,7-6,13-11 |
| ATP Antwerp - MD | 2023/10/18 10:15 | Tsitsipas/Tsitsipas v Middelkoop/Mies | 7-5,6-3 |
| ATP Antwerp - MD | 2023/10/17 10:30 | Reyes-Varela/Vega Hernandez v Tsitsipas/Tsitsipas | 6-7,6-7 |
| Puchar Davisa | 2023/09/17 08:00 | Tsitsipas/Tsitsipas v Klein/Zelenay | 3-6,7-6,3-6 |
| US Open - MD | 2023/09/02 16:00 | Tsitsipas/Tsitsipas v Dodig/Krajicek | 5-7,7-6,4-6 |
| US Open - MD | 2023/08/31 15:00 | Tsitsipas/Tsitsipas v Reyes-Varela/Vega Hernandez | 7-6,6-4 |